6-Fluoroisatoic anhydride → 6-Amino-3-bromo-2-methoxy-N-methylbenzamide

HRID 2279797Notes

Reaction equation

HRID 2279797 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6](F)[C:5]([Br:13])=[CH:4][CH:3]=1.FC1C2C(=O)[O:22][C:21](=O)NC=2C=CC=1.COC1C2C(=O)OC(=O)NC=2C=CC=1>>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[C:6]([O:22][CH3:21])[C:5]([Br:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 27830576-Fluoroisatoic anhydrideHCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione2×HCID 866977326-amino-3-bromo-2-fluoro-N-methylbenzamide

Product 1

HCID 866977426-Amino-3-bromo-2-methoxy-N-methylbenzamide

Procedure

Prepared analogously to Compound 27D replacing 5-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 27E) with 5-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (Compound 30E). 1H NMR (CDCl3, 500 MHz) δ 2.98 (d, J=4.5 Hz, 3H), 3.77 (s, 3H), 5.82 (br.s, 2H), 6.74 (d, J=9.0 Hz, 1H), 7.27 (d, J=9.0 Hz, 1H), 7.58 (br.s, 1H).

Sources & evidence

ORD record
ord-67dec46c542644e3a3e79eecb73e01f3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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