Hydrogen Bromide → 1-(3-(Bromomethyl)-4-methoxy-5-methylphenyl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amine

HRID 1662202Notes

Reaction equation

HRID 1662202 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:11])[C:4]([C:24]2[CH:25]=[C:26]([CH3:34])[C:27]([O:32][CH3:33])=[C:28]([CH2:30]O)[CH:29]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[N:22][CH:23]=3)[CH:13]=2)[N:3]=1.[BrH:35].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:35][CH2:30][C:28]1[CH:29]=[C:24]([C:4]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[CH:23]=[N:22][CH:21]=[N:20][CH:19]=4)[CH:13]=3)[C:5]3[C:10](=[C:9]([F:11])[CH:8]=[CH:7][CH:6]=3)[C:2]([NH2:1])=[N:3]2)[CH:25]=[C:26]([CH3:34])[C:27]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 58579497(5-(3-Amino-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-1-yl)-2-methoxy-3-methylphenyl)methanol

Product 1

HCID 585794761-(3-(Bromomethyl)-4-methoxy-5-methylphenyl)-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-3-amineYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-(3-amino-4-fluoro-1-(3-(pyrimidin-5-yl)phenyl)-1H-isoindol-1-yl)-2-methoxy-3-methylphenyl)methanol (250 mg, 0.55 mmol) in DCM (5 mL) was added HBr (33% in acetic acid) (5 mL, 92.08 mmol) and the mixture was stirred at rt over night. Aqueous Na2CO3 was added to the mixture to reach pH ˜9. The water layer was extracted with DCM and the combined extracts were dried (MgSO4) and concentrated under reduced pressure to afford 185 mg (65%) of the title compound. MS (ES+) m/z 517, 519 [M+H]+.

Workup

  1. extractionThe water layer was extracted with DCM
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e16cfcbf3e79469da8e462be064703a2
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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