Potassium Carbonate → 4-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester

HRID 1406256Notes

Reaction equation

HRID 1406256 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:27][CH:28]([CH3:33])[CH2:29]B(O)O.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:27][CH:28]([CH3:33])[CH3:29])[C:11]2[C:16]([C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734395(2-Methylpropyl)boronic acidHCID 860145034-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667132624-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester (207 mg, 0.5 mmol, see example D-86a), Pd(PPh3)4 (58 mg, 0.05 mmol), 2-methylpropylboronic acid (78 mg, 0.75 mmol), K2CO3 (207 mg, 1.5 mmol), and 1,4-dioxane (4 ml) was refluxed with stirring for 48 h. Subsequently, the mixture was concentrated in vacuo. To the residue was added water (5 ml) and the mixture was extracted with EtOAc (2×20 ml). The organic phase was dried over MgSO4 and evaporated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes EtOAc=88 12 as the eluent gave the title compound as a yellowish oil (136 mg); MS-(+)-ion M+1=392.3.

Workup

  1. temperaturewas refluxed
  2. concentrationSubsequently, the mixture was concentrated in vacuo
  3. additionTo the residue was added water (5 ml)
  4. extractionthe mixture was extracted with EtOAc (2×20 ml)
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-2baac160c0ad4e1e919273fcf70ffd85
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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