1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amine

HRID 1921794Notes

Reaction equation

HRID 1921794 reaction equation
OC1C=CC(CNC(=O)C2C=CC(NC3C4N(C=CN=4)C(C4C=NNC=4)=CN=3)=CC=2)=CC=1.[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37](Br)=[N:36][CH:35]=1.[CH3:44][N:45]1[N:49]=[N:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=2)=[N:46]1.CC([O-])(C)C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:56][C:53]2[CH:54]=[CH:55][C:50]([C:47]3[N:48]=[N:49][N:45]([CH3:44])[N:46]=3)=[CH:51][CH:52]=2)=[N:36][CH:35]=1

Participants

8

Reactant 5

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11328464-(2-methyl-2H-1,2,3,4-tetrazol-5-yl)anilineHCID 23676156Sodium t-butoxideHCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamideHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 59023119(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(2-methyl-2H-tetrazol-5-yl)-phenyl]-amineYield 44.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (334 mg, 1.21 mmol), 4-(2-methyl-2H-tetrazol-5-yl)-phenylamine (211.1 g, 1.21 mmol), NaOtBu (162 mg, 1.69 mmol), Pd2(dba)3 (44.1 mg, 0.0482 mmol), Xantphos (55.8 mg, 0.0964 mmol) and toluene (16 mL). The crude product is purified by silica gel column chromatography eluting with a 8:2:1 mixture petroleum ether:EtOAc:MeOH to afford the title compound as a yellow solid (198 mg, 44%).

Workup

  1. customThe crude product is purified by silica gel column chromatography
  2. washeluting with a 8:2:1 mixture petroleum ether

Sources & evidence

ORD record
ord-572b271189b9451a845a778c86819925
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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