Boron tribromide → 3-[8-(Cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]phenol

HRID 456699Notes

Reaction equation

HRID 456699 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][CH:19]=[C:18]([O:22]C)[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]=[C:18]([OH:22])[CH:19]=[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 10139996N-Cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-8-amine

Product 1

HCID 101390603-[8-(Cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]phenolYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (−78° C.) solution of formed N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-8-amine (42 mg, 0.09 mmol) in dichloromethane (5 mL) was added boron tribromide (0.5 mL, 1 M in dichloromethane, 0.5 mmol) dropwise. The solution was allowed to warm to room temperature over 4 hours and stirred for an additional 16 hours. The reaction was quenched by the addition of methanol followed by saturated aqueous sodium bicarbonate. Ether was added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 hexanes:ethyl acetate) provided 3-{8-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]imidazo[1,2-α]pyridin-2-yl}phenol (30 mg, 73%) as a yellow solid. 1H NMR (CDCl3): δ 8.90 (broad, 1H), 7.96 (d, 1H), 7.31 (s, 1H), 7.17 (t, 1H), 7.01 (d, 1H), 6.81–6.75 (m, 2H), 6.38 (d, 1H), 6.27 (d, 1H), 5.53 (d, 1H), 5.28 (d, 1H), 4.30 (m, 1H), 3.88 (m, 1H), 2.10–1.93 (m, 4H), 1.78–1.48 (m, 12H); MS m/z 455 (M+1).

Workup

  1. customThe reaction was quenched by the addition of methanol
  2. additionEther was added
  3. customthe layers separated
  4. washThe organic layer was washed with brine
  5. extractionThe aqueous layer was extracted with ether
  6. dry with materialthe combined organics were dried over magnesium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-92728eaf1daf474797e8849d9c4f7203
Source dataset
uspto-grants-2007_03
Patent number
US07186714B2

Reaction notes

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