(3-Cyano-5-fluorophenyl)boronic acid → 3-[(4,4-diethyl-1-methyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)amino]-5-fluorobenzonitrile

HRID 899203Notes

Reaction equation

HRID 899203 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[CH:17]=1.[F:18][C:19]1[CH:20]=[C:21]([C:28]#[N:29])[CH:22]=[C:23](B(O)O)[CH:24]=1>>[CH2:13]([C:7]1([CH2:15][CH3:16])[C:6]2[CH:17]=[C:2]([NH:1][C:23]3[CH:22]=[C:21]([CH:20]=[C:19]([F:18])[CH:24]=3)[C:28]#[N:29])[CH:3]=[CH:4][C:5]=2[N:10]([CH3:11])[C:9](=[O:12])[O:8]1)[CH3:14]

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 692163266-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 113141843-[(4,4-diethyl-1-methyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)amino]-5-fluorobenzonitrile

Procedure

Prepared from 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and 5-fluoro-3-cyanophenylboronic acid according to the coupling protocol of example 1. 1H NMR (DMSO-d6): δ 8.74 (s, 1H), 7.20 (dd, J=8.6, 2.3 Hz, 1H), 7.09 (m, 2H), 7.02 (m, 1H), 6.99 (d, J=2.4 Hz, 1H), 6.94 (dt, J=11.7, 2.2 Hz, 1H), 3.28 (s, 3H), 2.01 (m, 4H), 0.82 (t, J=8.3 Hz, 6H); MS (ESI) m/z 354 ([M+H]+); MS (ESI) m/z 352 ([M−H]−). Anal. calcd for C20H20FN3O2: C, 67.97; H, 5.70; N, 11.89. Found: C, 64.95; H, 5.42; N, 11.05.

Sources & evidence

ORD record
ord-9ea787ed753b47de88b6098eaeb1d2d1
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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