3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → HCID 11234373, compound

HRID 1296504Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH3:11])[C:9](=[O:12])[O:8][C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]=2[C:17]=1[F:18].[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[F:26]>>[Cl:19][C:20]1[CH:21]=[C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[N:10]([CH3:11])[C:9](=[O:12])[O:8][C:7]([CH2:13][CH3:14])([CH2:15][CH3:16])[C:6]=3[C:17]=2[F:18])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)

HCID 69213315HCID 69213315, compound

Product 1

HCID 11234373HCID 11234373, compound

Procedure

Prepared from 6-amino-4,4-diethyl-5-fluoro-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and 3-chloro-4-fluorophenylboronic acid according to the coupling procedure described in example 1. 1H NMR (DMSO-d6): δ 8.03 (s, 1H), 7.32 (t, J=8.8 Hz, 1H), 7.26 (t, J=9.1 Hz, 1H), 6.92 (m, 2H), 6.83 (m, 1H), 3.29 (s, 3H), 2.12 (m, 2H), 1.92 (m, 2H), 0.84 (t, J=7.2 Hz, 6H); MS (ESI) m/z 381/383 ([M+H]+); MS (ESI) m/z 379/381 ([M−H]−); Anal. calcd for C19H19ClF2N2O2: C, 59.93; H, 5.03; N, 7.36. Found: C, 59.68; H, 4.92; N, 7.14.

Sources & evidence

ORD record: ord-368589c793b34eb7a4466217779642ef
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247625B2

Reaction notes

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