Bromomethylcyclopropane → Methyl 4-(3,5-dichloro-4-(cyclopropylmethoxy)benzamido)benzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:22])[C:20]=1[OH:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=[O:6].Br[CH2:24][CH:25]1[CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:22])[C:20]=1[O:21][CH2:24][CH:25]1[CH2:27][CH2:26]1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)=[O:6]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
Methyl 4-(3,5-dichloro-4-(cyclopropylmethoxy)benzamido)benzoate (6) (120 mg, 100%) was prepared from methyl 4-(3,5-dichloro-4-hydroxybenzamido)benzoate (5) (100 mg, 294 μmol) and (bromomethyl)cyclopropane (57 μL, 588 μmol) using a procedure essentially the same as in Step (i) for AAA-001 except the mixture was stirred at 50° C. for 18 h: m/z 392 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.99 (4H, d), 7.85 (2H, d), 3.99 (2H, d), 3.90 (3H, s), 1.49-1.29 (1H, m), 0.65-0.60 (2H, m), 0.37-0.34 (2H, m).
Sources & evidence
- ORD record
- ord-97f344d81b284ed091b8f53dade8b4f4
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447028B2
Reaction notes
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