Ethanol → HCID 86761495, compound

HRID 1642416Notes

Reaction equation

HRID 1642416 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[S:26][CH:25]=[CH:24][N:19]3[C:20](=[O:23])[C:21]=2I)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:33](O)[CH3:34].O>C1(C)C=CC=CC=1>[CH3:16][N:17]([CH3:18])[C:34]1[CH:33]=[CH:3][C:2]([C:21]2[C:20](=[O:23])[N:19]3[CH:24]=[CH:25][S:26][C:18]3=[N:17][C:16]=2/[CH:15]=[CH:14]/[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:6]=2[O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:1][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 66753592HCID 66753592, compound

Product 1

HCID 86761495HCID 86761495, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared from Intermediate 2 (150 mg, 31 mmol), 4-N,N-dimethylaminophenylboronic acid (61 mg, 37 mmol), Pd[(C6H5)3P]4 (61 mg, 37 mmol) and sodium carbonate (206 mg, 1.91 mmol) in a mixture of toluene, ethanol and water according to the procedure outlined in Example 1 to afford a crude product which was purified by silica gel column chromatography using 10% ethyl acetate in chloroform to give 110 mg of the product; 1H NMR (300 MHz, DMSO-d6) δ 0.26-0.28 (m, 1H), 0.50 (d, J=7.8 Hz, 2H), 1.06-1.08 (m, 1H), 6.77 (d, J=8.4 Hz, 2H), 6.88-6.90 (m, 1H), 6.97-7.04 (m, 3H), 7.14 (d, J=5.1 Hz, 2H), 7.95 (d, J=5.1 Hz, 1H), 8.10 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 474.19 (M+H)+.

Workup

  1. customto afford a crude product which

Sources & evidence

ORD record
ord-5367e9982246428d92a76ebe0e9aefe6
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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