Pyridine → HCID 70229768, compound

HRID 1978034Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH:8]=[CH:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)([CH3:4])[CH3:3].N1C=CC=CC=1.[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>ClCCl.O>[CH3:4][C:2]([Si:5]([CH3:18])([CH3:19])[O:6][CH2:7][CH:8]=[CH:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:33](=[O:34])[C:32]2[CH:36]=[CH:37][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:30][CH:31]=2)=[CH:13][CH:12]=1)([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A 0° C. solution of Example 126B (0.92 g, 3.0 mmol) in dichloromethane (10 mL) was sequentially treated with pyridine (0.3 mL, 3.7 mmol) and 4-trifluoromethoxybenzoyl chloride (0.53 mL, 3.4 mmol), stirred at 0° C. for 0.5 hours and then at room temperature for 1 hour. The reaction was diluted with water and extracted with dichloromethane (3×15 mL). The combined extracts were washed with saturated NaHCO3, dried, filtered, concentrated and purified on silica gel by flash column chromatography eluting with 6:1 hexanes/ethyl acetate to give 1.37 g of the desired product. MS (ESI): 501 (M+NH4+), 506 (M+Na+).

Workup

waitat room temperature for 1 hour
extractionextracted with dichloromethane (3×15 mL)
washThe combined extracts were washed with saturated NaHCO3
customdried
filtrationfiltered
concentrationconcentrated
custompurified on silica gel by flash column chromatography
washeluting with 6:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-2a0258221fa945b88653195dda55bcfd
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235786B1

Reaction notes

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