Triethylamine → N-(6-Bromo-5-methoxypyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 1442792Notes

Reaction equation

HRID 1442792 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].CCN(CC)CC.[F:18][C:19]1([F:34])[O:23][C:22]2[CH:24]=[CH:25][C:26]([C:28]3([C:31](Cl)=[O:32])[CH2:30][CH2:29]3)=[CH:27][C:21]=2[O:20]1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:31]([C:28]2([C:26]3[CH:25]=[CH:24][C:22]4[O:23][C:19]([F:34])([F:18])[O:20][C:21]=4[CH:27]=3)[CH2:30][CH2:29]2)=[O:32])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127582096-Bromo-5-methoxypyridin-2-amineHCID 575168501-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 59165869N-(6-Bromo-5-methoxypyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-bromo-5-methoxypyridin-2-amine (510 mg, 2.5 mmol) and Et3N (690 μL, 4.9 mmol) in dichloromethane (10 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (650 mg, 2.5 mmol) in dichloromethane (5 mL). The resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was then washed with 1N HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL). The organics were dried over sodium sulfate and evaporated to yield the product (850 mg, 81%). ESI-MS m/z calc. 426.0, found 427.3 (M+1)+. Retention time 2.05 minutes.

Workup

  1. customThe resulting reaction mixture
  2. washThe reaction mixture was then washed with 1N HCl (1×20 mL) and saturated aqueous NaHCO3 (1×20 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3488a7539fc14a959014e5ee95b7ab6c
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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