3-(Trifluoromethyl)phenylboronic acid → HCID 70008710, compound

HRID 1266021Notes

Reaction equation

HRID 1266021 reaction equation
I[C:2]1[C:3]([CH3:16])=[C:4]2[C:8]3=[C:9]([CH2:11][NH:12][CH2:13][C:14](=[O:15])[N:7]3[CH:6]=[CH:5]2)[CH:10]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>>[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[C:23]([C:2]2[C:3]([CH3:16])=[C:4]3[C:8]4=[C:9]([CH2:11][NH:12][CH2:13][C:14](=[O:15])[N:7]4[CH:6]=[CH:5]3)[CH:10]=2)[CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 69701249HCID 69701249, compound

Product 1

HCID 70008710HCID 70008710, compoundYield 81%

Procedure

Using the procedure described in Example 50(b), the title compound was synthesized from 6-iodo-7-methyl-3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 50(a)) and 3-trifluoromethylphenylboronic acid in 81% yield after purification by preparative HPLC. A gradient mobile phase, starting with 90% 0.1M NH4OAc, 10% CH3CN up to 2 min, then reaching 100% CH3CN after 22 min, was used. Rt=17.59 min. The title compound was obtained in the form of a white solid: 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 3.44-3.48 (m, 2H), 4.13-4.16 (m, 2H), 7.19 (t, 1H, J=7.5 Hz), 7.77-7.88 (m, 6H), 8.32-8.36 (m, 1H). HRMS calcd. for C19H15N2OF3 (M+) 344.136, found 344.1136. Anal. HPLC Rt=14.9 min.

Workup

  1. customafter purification by preparative HPLC
  2. customafter 22 min
  3. customThe title compound was obtained in the form of a white solid

Sources & evidence

ORD record
ord-2067d11ac597466c9fdf6816689f89fe
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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