tert-Butyl bromoacetate → tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate

HRID 2260984Notes

Reaction equation

HRID 2260984 reaction equation
[CH3:1][C:2]1([CH3:20])[C:7]2[CH:8]=[C:9]([C:12]3[NH:16][C:15]([C:17]#[N:18])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:19])[O:3]1.[C:21]([O:25][C:26](=[O:29])[CH2:27]Br)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:29])[CH2:27][N:16]1[C:12]([C:9]2[CH:10]=[CH:11][C:6]3[NH:5][C:4](=[O:19])[O:3][C:2]([CH3:20])([CH3:1])[C:7]=3[CH:8]=2)=[CH:13][CH:14]=[C:15]1[C:17]#[N:18])([CH3:24])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 102209945-(4,4-Dimethyl-oxo-1,4-dihydro-2H-3,1-benzoxazine-6-yl)-1H-pyrrole-carbonitrile

Product 1

HCID 12044964tert-butyl[2-cyano-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-1-yl]acetate

Procedure

5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrol-2-carbonitrile (5.4 g, 20 mmol) and tert-butylbromoacetate (4.64 g, 22 mmol) were reacted, according to General Method A, to afford the title compound, m.p. 188-190° C. (3 g, 40%). 1H-NMR (DMSO-d6) δ 1.35 (s, 9H), 1.62 (s, 6H), 4.8 (s, 2H), 6.35 (d, J=4.3 Hz, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.09 (d, J=4.3 Hz, 1H), 7.26 (m, 2H), 10.42 (s, 1H), MS (APCI (−)) m/z 380 (M−H)−

Sources & evidence

ORD record
ord-f1c6a9af51f24ba78a5bd010437fba44
Source dataset
uspto-grants-2010_12
Patent number
US07846924B2

Reaction notes

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