Dimethylformamide → 6-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

HRID 906420Notes

Reaction equation

HRID 906420 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]([CH3:30])([CH3:29])[CH2:20]O[Si](C(C)(C)C)(C)C)[CH:11]=[CH:10]2.CN([CH:34]=[O:35])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][C:19]([CH3:29])([CH3:30])[CH2:20][Cl:3])[CH:11]=[C:10]2[CH:34]=[O:35]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 671303156-Bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)isoquinolin-1(2H)-one

Product 1

HCID 866409616-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

Procedure

Phosphorus oxychloride (104 mL) was added to an ice cooled solution of DMF (180 mL) over 1 h and the resulting mixture stirred at room temperature for 1.5 h before adding dropwise to a solution of 6-bromo-2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)isoquinolin-1(2H)-one (Example 26b, 31.7 g) in DMF (70 mL) under nitrogen. The resulting solution was stirred at 85° C. for 20 h. The cooled reaction mixture was poured onto ice/water (2 L) and stirred for 1 h.

Workup

  1. stirringThe resulting solution was stirred at 85° C. for 20 h
  2. customThe cooled reaction mixture
  3. additionwas poured onto ice/water (2 L)
  4. stirringstirred for 1 h.

Sources & evidence

ORD record
ord-b910bd87889044eda76eda134e19d802
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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