Sodium Carbonate → HCID 57870509, compound

HRID 1661201Notes

Reaction equation

HRID 1661201 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[N:10]=[CH:9]2)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57870506HCID 57870506, compound

Product 1

HCID 57870509HCID 57870509, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 7 (250 mg, 0.76 mmol), phenylboronic acid (102 mg, 0.84 mmol) and Na2CO3 (244 mg, 2.3 mmol) in DME/H2O 4:1 (10 mL) was thoroughly purged with argon, after which Pd(PPh3)2Cl2 (36 mg; 0.05 mmol) was added and the mixture was heated to 70° C. for 21 h. The solvents were removed in vacuo and the residue was purified by column chromatography (1 to 5% methanol in CH2Cl2 to give 100 mg (41%) pure 8. HRMS (ESI+): m/z=324.3814 [M+H]

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by column chromatography (1 to 5% methanol in CH2Cl2
  3. customto give 100 mg (41%) pure 8

Sources & evidence

ORD record
ord-b8a37b0acd014dbcbf41e5cb0ee5c09c
Source dataset
uspto-grants-2011_10
Patent number
US08030339B2

Reaction notes

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