Boron tribromide → HCID 59222981, compound

HRID 1467405Notes

Reaction equation

HRID 1467405 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)=[C:18]([O:33]C)[CH:17]=1)=[N:5][CH:6]=[N:7]2.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[CH:25][N:24]=3)=[C:18]([OH:33])[CH:17]=1)=[N:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 46184151HCID 46184151, compound

Product 1

HCID 59222981HCID 59222981, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5,8-difluoroquinazolin-4-yl)-{2-[3-methoxy-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine (2.71 g, 5.69 mmol) in CH2Cl2 (25 mL) cooled to −50° C., was added 1 M BBr3 in CH2Cl2 (17 mL, 17 mmol). The solution was allowed to warm to room temperature and stirred overnight, and then quenched slowly with methanol. The solvent was removed by rotary evaporation and the residue was suspended in chloroform. The product was collected by suction filtration to give 2.70 g (quantitative) of 5-[2-(5,8-difluoroquinazolin-4-ylamino)-ethyl]-2-(4-trifluoromethylpyridin-2-yloxy)-phenol. The product was used in the following reaction without further purification. 1H NMR (CD3OD): δ 8.78 (s, 1H), 8.39 (d, J=5.4 Hz, 1H), 7.93 (m, 1H), 7.54 (m, 1H), 7.45 (d, J=5.4 Hz, 1H), 7.19 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H) 6.87 (dd, J=7.8, 2.1 Hz, 1H), 4.12 (t, J=7.5 Hz, 2H), 3.05 (t, J=7.5 Hz, 2H). LC/MS: 460.97 (M+−1).

Workup

  1. customquenched slowly with methanol
  2. customThe solvent was removed by rotary evaporation
  3. filtrationThe product was collected by suction filtration

Sources & evidence

ORD record
ord-0c73350849d041c0980b7aeb0d1f8676
Source dataset
uspto-grants-2015_04
Patent number
US09000162B2

Reaction notes

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