Boron tribromide → HCID 135450042, compound

HRID 456694Notes

Reaction equation

HRID 456694 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]3[N:9]([C:13]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[N:25]=4)=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=4)[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([NH:6][C:7]2[C:8]3[N:9]([C:13]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[N:25]=4)=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=4)[N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10162184HCID 10162184, compound

Product 1

HCID 135450042HCID 135450042, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-methoxyphenyl)imidazo[1,2-α]pyridin-8-amine (0.4 g, 0.9 mmol) in dichloromethane (10 mL) at −78° C. was added boron tribromide (2.6 mL, 1.0 M in dichloromethane, 2.6 mmol) dropwise. The resulting solution was allowed to warm to room temperature. After stirring for 15 hours at room temperature, the mixture was cooled to 0° C. and quenched by the addition of water and aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid residue which was purified by silica gel chromatography (95:5 chloroform-methanol) to give 4-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}phenol as a solid (280 mg, 70%). 1H NMR (DMSO-d6): δ 9.63 (s, 1H), 8.86 (broad s, 1H), 8.07 (d, 1H), 7.37 (d, 2H), 7.30 (d, 1H), 6.80 (m, 3H), 6.30 (m, 2H), 5.60 (d, 1H), 4.19 (m, 1H), 3.89 (m, 1H), 1.9–2.1 (m, 4H), 1.4–1.9 (m, 12H); MS m/z 455 (M+1).

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customquenched by the addition of water and aqueous sodium bicarbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid residue which
  8. customwas purified by silica gel chromatography (95:5 chloroform-methanol)

Sources & evidence

ORD record
ord-81ea3a318eb74188a6111582210f8c46
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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