Ethanol → HCID 59187437, compound

HRID 1944504Notes

Reaction equation

HRID 1944504 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3Br)[N:18]=2)=[CH:8][C:7]=1[CH3:26].[CH:28]1(B(O)O)[CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O.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.COCCOC>[CH:28]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:17]2[N:18]=[C:14]([CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([O:2][CH3:1])=[O:27])=[C:7]([CH3:26])[CH:8]=3)[S:15][CH:16]=2)[CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 59187439HCID 59187439, compound

Product 1

HCID 59187437HCID 59187437, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

{4-[4-(2-Bromo-phenyl)-thiazol-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester (30 mg, 0.067 mmol), cyclopropylboronic acid (6.9 mg, 0.080 mmol) and sodium carbonate (21 mg, 0.20 mmol) are dissolved in water (120 μL), ethanol (90 μL) and 1,2-dimethoxyethane (360 μL). Pd(PPh3)4 (10 mol %) is added, and the mixture is subjected to microwave (180° C.) for 5 min in a sealed tube to give crude methyl 2-(4-((4-(2-cyclopropylphenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetate, which is used without further purification in Step B.

Workup

  1. custom(180° C.)
  2. customfor 5 min

Sources & evidence

ORD record
ord-d1f2e14203aa419596a68554afb76f22
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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