1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amine

HRID 1366163Notes

Reaction equation

HRID 1366163 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]([CH2:47][C:48]1[N:49]=[N:50][N:51]([C:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=2)[CH:52]=1)[CH3:46].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:59][C:56]2[CH:55]=[CH:54][C:53]([N:51]3[CH:52]=[C:48]([CH2:47][N:45]([CH3:46])[CH3:44])[N:49]=[N:50]3)=[CH:58][CH:57]=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 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]pyrazineHCID 590230944-(4-Dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamine

Product 1

HCID 59023092(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-amineYield 36.1%

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 (116.9 mg, 0.422 mmol), 4-(4-dimethylaminomethyl-[1,2,3]triazol-1-yl)-phenylamine (91.7 g, 0.422 mmol), NaOtBu (56.8 mg, 0.591 mmol), Pd2(dba)3 (15.5 mg, 0.0169 mmol), Xantphos (19.5 mg, 0.0337 mmol) and toluene (5 mL). The crude product is purified by Isolute FlashSilicaII cartridge chromatography eluting with 99:1 DCM/NH3 (7M in MeOH), followed by 97:3 DCM:NH3 (7M in MeOH). The title compound (63 mg, 36%) is isolated after a second column chromatography purification eluting with 97:3 DCM:NH3 (7M in MeOH).

Workup

  1. customThe crude product is purified by Isolute FlashSilicaII cartridge chromatography
  2. washeluting with 99:1 DCM/NH3 (7M in MeOH)

Sources & evidence

ORD record
ord-b44d5e57438541149bbca54503f37e83
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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