Sodium Carbonate → tert-butyl 5-(3-(4-(1H-pyrazol-4-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

HRID 1518355Notes

Reaction equation

HRID 1518355 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:35][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][C:42](I)=[CH:41][CH:40]=3)=[C:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].CC1(C)C(C)(C)OB([C:62]2[CH:63]=[N:64][NH:65][CH:66]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.O>[NH:64]1[CH:63]=[C:62]([C:42]2[CH:43]=[CH:44][C:39]([O:38][CH2:37][CH2:36][CH2:35][C:25]3[S:24][C:23]([N:20]4[CH2:19][CH2:18][C:17]5[C:22](=[C:13]([C:11](=[O:12])[N:10]([C:2]6[S:1][C:5]7[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=7[N:3]=6)[CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:52])([CH3:51])[CH3:53])[CH:14]=[CH:15][CH:16]=5)[CH2:21]4)=[N:27][C:26]=3[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[CH:40][CH:41]=2)[CH:66]=[N:65]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59447531tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-(4-iodophenoxy)propyl)thiazole-4-carboxylate

Product 1

HCID 59447632tert-butyl 5-(3-(4-(1H-pyrazol-4-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A mixture of compound 41A (90 mg, 0.102 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (29.7 mg, 0.153 mmol), Na2CO3 (108 μl, 0.102 mmol) (1M) and (Ph3P)2Cl2Pd (7.15 mg, 10.19 μmol) in EtOH-DME-H2O (7:3:2, 4 ml) was in a Smith microwave synthesizer at 120° C. for 30 min and then concentrated. The residue was purified by flash chromatography to give the compound 73A. LCMS (APCI) m/e 824 (M+H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8466ff8c6d664211895a464c5a0e6e55
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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