Sodium Carbonate → HCID 58487083, compound

HRID 874624Notes

Reaction equation

HRID 874624 reaction equation
[CH3:1][N:2]1[C:6](B(O)O)=[CH:5][C:4]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[N:3]1.[NH2:15][C:16]1[N:21]=[C:20]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[O:24])[CH:19]=[CH:18][C:17]=1Br.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CCO.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>[NH2:15][C:16]1[N:21]=[C:20]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[O:24])[CH:19]=[CH:18][C:17]=1[C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 58486936HCID 58486936, compoundHCID 58487036HCID 58487036, compound

Product 1

HCID 58487083HCID 58487083, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

The boronic acid 91 (19.2 mg, 0.1 mmol) and 61 (31 mg, 0.1 mmol) was dissolved in 1 mL dimethoxyethane and 1 mL EtOH. The 0.5 ml of 2 M Na2CO3 was added and the mixture was bubbled with Ar for 1 min before add tetrakis(triphenylphosphine)-pallacium(0) (Pd(Ph3P)4, 11 mg, 0.01 mmol). The reaction was heated at 110° C. for 30 min under microwave initiator. The reaction mixture was worked-up with EtOAc extraction and product was purified by HPLC and afforded 100 (10.8 mg, 29%) as white solid. LC-MS: calcd. for C20H16FN5O2: 378 (M+1).

Workup

  1. customthe mixture was bubbled with Ar for 1 min
  2. extractionThe reaction mixture was worked-up with EtOAc extraction and product
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-dccb9b91f994406ca1d0ac6f65c646a8
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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