Sodium Chloride → [2-(7-Phenyl-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

HRID 2219199Notes

Reaction equation

HRID 2219199 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([O:11][C:12](=[O:31])[NH:13][CH2:14][CH2:15][NH:16][S:17]([C:20]1[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][C:26]=2[CH:27]=[C:28](Br)[CH:29]=1)(=[O:19])=[O:18])([CH3:10])([CH3:9])[CH3:8].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Na+].[Cl-]>O1CCOCC1.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.C(Cl)Cl.CCOC(C)=O>[C:7]([O:11][C:12](=[O:31])[NH:13][CH2:14][CH2:15][NH:16][S:17]([C:20]1[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][C:26]=2[CH:27]=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:29]=1)(=[O:19])=[O:18])([CH3:10])([CH3:9])[CH3:8]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58816140[2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69275032[2-(7-Phenyl-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

An aqueous Na2CO3 solution (2M, 7.22 mL) is added to a stirred solution of [2-(7-bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (3.03 g, 7.04 mmol), phenylboronic acid (0.876 g, 7.18 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.407 g, 0.352 mmol) in 1,4-dioxane (36 mL) at ambient temperature under argon. The resultant mixture is heated at 95° C. for 24 hours. At ambient temperature, EtOAc (200 mL)/CH2Cl2 (50 mL) and half-saturated aqueous NaCl solution (200 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. After chromatography on silica gel (gradient 0-3% CH3OH in CH2Cl2), 2.83 g (6.62 mmol, 94% yield) of the title compound is obtained as a white solid. ESIMS: m/z 428 (M+H)+.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18db4ed863f7456ca40ba002cfc2276c
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

Loading…