2-[2-(Cyclopropylmethoxy)-4,5-difluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 90407657, compound

HRID 2277539Notes

Reaction equation

HRID 2277539 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[N:12]=[CH:13][N:14]([CH3:17])[C:15]=2Br)[CH:6]=1)=[O:4].[CH:18]1([CH2:21][O:22][C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=2B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][O:22][C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=2[C:15]2[N:14]([CH3:17])[CH:13]=[N:12][C:11]=2[C:7]2[CH:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][N:8]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 665217732-[2-(Cyclopropylmethoxy)-4,5-difluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 90407023HCID 90407023, compound

Product 1

HCID 90407657HCID 90407657, compoundYield 5%

Procedure

The title compound was prepared in 5% yield from 2-(5-bromo-1-methyl-1H-imidazol-4-yl)pyridine-4-carboxylic acid methyl ester and 2-(cyclopropylmethoxy)-4,5-difluorophenylboronic acid pinacol ester according to the procedure for the preparation of Example 3, part A followed by hydrolysis. 1H NMR (400 MHz, DMSO-d6): δ 0.29-0.32 (2H, m), 0.53-0.58 (2H, m), 1.22 (1H, m), 3.43 (3H, s), 3.82 (2H, d, J=7.0 Hz), 6.82 (1H, br s), 7.09-7.14 (1H, m), 7.27 (1H, t, J=7.7 Hz), 7.42 (1H, d, J=3.6 Hz), 7.90 (1H, s), 8.20 (1H, d, J=4.3 Hz), 8.30 (1H, s). [M+H] Calc'd for C20H12F2N3O3, 386. Found, 386.

Workup

  1. customA followed by hydrolysis

Sources & evidence

ORD record
ord-1859f8b171da44449a6c4c4437337593
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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