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Potassium Carbonate → HCID 89815629, compound

HRID 2172281
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Reaction equation

HRID 2172281 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1I.CC1(C)C(C)(C)OB([C:21]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:22]=2[CH2:23][CH2:24][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]3)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(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>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH2:23][CH2:24][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 57505885tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 89815629HCID 89815629, compoundYield 85.9%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of Pd(PPh3)4 (Strem Chemicals Inc., Newburyport, Mass., 0.804 g, 0.696 mmol), 2-bromo-1-iodo-4-(trifluoromethyl)benzene (Matrix Scientific, Columbia, S.C., 3.05 g, 8.70 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (ASW Medchem, Brunswick, N.J., 2.500 g, 6.96 mmol), and potassium carbonate (4.81 g, 34.8 mmol) in 14 mL dioxane and 6 mL water was heated to 100° C. overnight. LC/MS showed about 50% conversion, so the reaction mixture was transferred to a microwave vial, and was heated to 130° C. in a microwave reactor for 3 hours. The reaction mixture was diluted with EtOAc, washed with water then brine, the organics dried over MgSO4 and concentrated. Purification of the resulting residue by silica gel column chromatography (0 to 30% EtOAc/heptane) gave tert-butyl 5-(2-bromo-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.73 g, 5.98 mmol).

Workup

  1. washwashed with water
  2. dry with materialbrine, the organics dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the resulting residue by silica gel column chromatography (0 to 30% EtOAc/heptane)

Sources & evidence

ORD record
ord-ea5e658ec6d144e38914f8a06de4dbd9
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051311B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes