3,4-Difluorobenzeneboronic acid → 6-(3,4-difluorophenylamino)-4,4-diethyl-1-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 899206Notes

Reaction equation

HRID 899206 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](B(O)O)[CH:22]=[CH:23][C:24]=1[F:25]>>[F:18][C:19]1[CH:20]=[C:21]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[N:10]([CH3:11])[C:9](=[O:12])[O:8][C:7]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]=3[CH:17]=2)[CH:22]=[CH:23][C:24]=1[F:25]

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 692163266-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 247586596-(3,4-difluorophenylamino)-4,4-diethyl-1-methyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Procedure

Prepared from 6-amino-4,4-diethyl-1-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and 3,4-difluorophenylboronic acid according to the coupling procedure described in example 1. 1H NMR (DMSO-d6): δ 8.24 (s, 1H), 7.28 (q, J=9.2 Hz, 1H), 7.11 (dd, J=8.7, 2.4 Hz, 1H), 7.02 (d, J=8.7 Hz, 1H), 6.90 (m, 2H), 6.74 (m, 1H), 3.26 (s, 3H), 1.97 (m, 4H), 0.81 (t, J=7.3 Hz, 6H). MS (ESI) m/z [M+H]+ (347); MS (ESI) m/z [M−H]−(345); Anal. calcd for C19H20F2N2O2: C, 65.88; H, 5.82; N, 8.09. Found: C, 65.30; H, 5.71; N, 7.79.

Sources & evidence

ORD record
ord-f1f898612ed942f0ad4ec8feff00803b
Source dataset
uspto-grants-2008_04
Patent number
US07354915B2

Reaction notes

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