Dichloromethane → HCID 67364390, compound

HRID 1914939Notes

Reaction equation

HRID 1914939 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C:8]2[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=3)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.ClCCl.[Br:29]Br>>[Br:29][C:20]1[C:21]([NH2:24])=[N:22][CH:23]=[C:18]([C:16]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[F:25])[CH:17]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 673640755-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-2-ylamine

Product 1

HCID 67364390HCID 67364390, compound

Procedure

To a solution of 429 mg (1.22 mmol) 5-[2-(5-Chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-2-ylamine in 5 ml dichloromethane 195 mg (1.84 mmol) sodium bicarbonate was added. Then 94 μl (1.84 mmol) bromine were added slowly. The reaction mixture was stirred for 1 hour at room temperature and subsequently was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated yielding 3-bromo-5-[2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-2-ylamine as brown amorphous solid; HPLC-MS: 2.18 min, [M+H] 431.

Workup

  1. customsubsequently was partitioned between water and dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-3c3a8a7a0fe449eda20292c102920545
Source dataset
uspto-grants-2013_12
Patent number
US08614226B2

Reaction notes

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