Sodium Methoxide → HCID 67316714, compound

HRID 503562Notes

Reaction equation

HRID 503562 reaction equation
C[O-].[Na+].Br[C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[N:25][N:24]=4)=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[N:7][CH:6]=1>CN(C=O)C.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>[N:12]1[C:13]2[C:8](=[N:7][CH:6]=[CH:5][CH:14]=2)[C:9]([O:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[N:25][N:24]=3)=[CH:20][CH:21]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67317785HCID 67317785, compound

Product 1

HCID 67316714HCID 67316714, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tetrakis(triphenylphosphine)palladium (9 mg, 0.0079 mmol) and sodium methoxide (9 mg, 0.16 mmol) was added a solution of N-(4-(7-bromo-1,5-naphthyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine (0.041 g, 0.079 mmol) in DMF (2 mL). The mixture was heated to 100° C. in an Argon purged, resealable tube. After 3 hrs, the solvent was removed in vacuo and the residue was purified by silica gel chromatography using 1-10% MeOH:CH2Cl2 containing 1% NH4OH to afford N-(4-(1,5-naphthyridin-4-yloxy)phenyl)-4-phenylphthalazin-1-amine as a tan solid. [email protected] min.

Workup

  1. custompurged
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bf9ddeefdb5d47669f4a8c357a32e092
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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