Sodium Carbonate → HCID 67433207, compound

HRID 1040008Notes

Reaction equation

HRID 1040008 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)([OH:9])[CH3:8])=[N:4][CH:3]=1.O.[NH2:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[NH2:24][C:25]1[CH:30]=[C:29]([C:2]2[S:6][C:5]([C:7]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)([OH:9])[CH3:8])=[N:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 67431988Tert-butyl 4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]piperidine-1-carboxylate

Product 1

HCID 67433207HCID 67433207, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The product of Step 2 (87 mg, 0.222 mmol), 3-aminophenylboronic acid monohydrate (41.3 mg, 0.267 mmol), Pd(Ph3P)4 (12.85 mg, 0.011 mmol) and Na2CO3 (0.333 mL, 0.667 mmol) were stirred in DME at 100° C. overnight under N2. The reaction mixture was filtered through a pre-pack pad of celica with dichloromethane. The filtrate was concentrated and the residue was purified by flash chromatography to give tert-butyl 4-{1-[5-(3-aminophenyl)-1,3-thiazol-2-yl]-1-hydroxyethyl}piperidine-1-carboxylate (82.4 mg, 0.204 mmol, 92%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through a pre-pack pad of celica with dichloromethane
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b935c3502d6c40d3b424907c9634c076
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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