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b) 1 -Benzyl- 1 H -pyrazole-4 -carbaldehyde (A 148) 1-Benzyl-4-iodo-1 H-pyrazole A147 (859 mg, 3.02 mmol) in THF (5 mL) was cooled to 0 C under nitrogen before a 2.0 M solution of isopropylmagnesium chloride in THF (1.66 mL, 3.33 mmol) was added. After 1 hour, DMF (0.5 mL) was added. The mixture was stirred for 30 minutes at 0 C then a further 30 minutes at room temperature. The mixture was quenched with a saturated aqueous solution of ammonium chloride (10 mL), diluted with water (20 mL) and extracted with CHCI3 (3 chi 25 mL). The pooled organics were washed with brine (50 mL), dried with sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (12 g Si02 cartridge, 0-50% EtOAc in hexanes) to give the title compound as a colourless oil (170 mg, 30%). H NMR (400 MHz, CDCI3) delta 9.83 (s, 1 H), 8.00 (s, 1 H), 7.88 (s, 1 H), 7.42-7.33 (m, 3H), 7.29-7.25 (m, 2H), 5.33 (s, 2H). LCMS-B: rt 3.10 min, m/z (positive ion) 187.1 [M+H]+.
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