Sodium Carbonate → HCID 69313528, compound

HRID 269985Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:17]([O:21][C:22](=[O:53])[N:23]([CH2:36][CH2:37][NH:38][S:39]([C:42]1[C:43]2[CH:44]=[CH:45][N:46]=[CH:47][C:48]=2[CH:49]=[C:50](Br)[CH:51]=1)(=[O:41])=[O:40])[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.CO.CCOC(C)=O>[C:17]([O:21][C:22](=[O:53])[N:23]([CH2:36][CH2:37][NH:38][S:39]([C:42]1[C:43]2[CH:44]=[CH:45][N:46]=[CH:47][C:48]=2[CH:49]=[C:50]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH:51]=1)(=[O:40])=[O:41])[CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 85 °C

Procedure

Add Pd(dppb)Cl2 (0.0051 g, 0.0085 mmol), 4-hydroxyphenylboronic acid (0.0258 g, 0.187 mmol) and 2M Na2CO3 (0.21 ml, 0.425 mmol) to [2-(7-bromo-isoquinoline-5-sulfonylamino)-ethyl]-[3-(4-nitro-phenyl)-propyl]-carbamic acid tert-butyl ester, (0.101 g, 0.170 mmol) in 3 ml DMF and 0.75 ml MeOH. Heat the reaction mixture at 85° C. for 1 h, then dilute with EtOAc (20 ml) and wash with H2O (2×20 ml) and brine (10 ml). Concentrate the organic layer and chromatograph on silica gel using a gradient of 0-2% MeOH in CH2Cl2 to give 0.093 g of {2-[7-(4-hydroxy-phenyl)-isoquinoline-5-sulfonylamino]-ethyl}-[3-(4-nitro-phenyl)-propyl]-carbamic acid tert-butyl ester, as a yellow solid in 90% yield. ES Positive Ion MS [M+H]+ ion observed: m/z 607. (Used in Example 98).

Workup

washwash with H2O (2×20 ml) and brine (10 ml)
concentrationConcentrate the organic layer and chromatograph on silica gel using a gradient of 0-2% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-cf33e236a34644c993a5357b36096ac6
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449477B2

Reaction notes

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