2-[(E)-2-(2,4-Difluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 53251101, compound

HRID 37796Notes

Reaction equation

HRID 37796 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:12]4.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1/[CH:26]=[CH:27]/B1OC(C)(C)C(C)(C)O1>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1/[CH:26]=[CH:27]/[C:2]1[C:10]2[NH:9][C:8]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:12]4

Participants

3

Reactant 2

HCID 162181542-[(E)-2-(2,4-Difluorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 53251101HCID 53251101, compound

Procedure

A suspension of the product of Example 1B (100 mg, 0.34 mmol) and trans-2-(2,4-difluorophenyl)vinylboronic acid pinacol ester (101 mg, 0.38 mmol; Aldrich) was processed as described in Example 4 to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ ppm 1.98-2.19 (m, 4 H), 3.03-3.17 (m, 3 H), 3.21-3.28 (m, 2 H), 4.24 (s, 2 H), 6.93-7.05 (m, 3 H), 7.25 (d, J=7.6 Hz, 1 H), 7.30 (d, J=16.2 Hz, 1 H), 7.37 (d, J=7.3 Hz, 1 H), 7.63 (d, J=16.5 Hz, 1 H), 7.79-7.88 (m, 1 H); MS (DCI) m/z 351 (M+H)+.

Sources & evidence

ORD record
ord-0b0514e413b245cab2a6a1abe9a874ec
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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