3-Bromoaniline → HCID 18473296, compound

HRID 2227258Notes

Reaction equation

HRID 2227258 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1(S(N2C3N=CN=C([Cl:35])C=3C(I)=C2)(=O)=O)C=CC=CC=1.BrC1C=C(B(O)O)C=CC=1.[Br:47][C:48]1[CH:49]=[C:50]([CH:52]=[CH:53][CH:54]=1)[NH2:51]>CO>[Br:47][C:48]1[CH:49]=[C:50]([NH:51][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([Cl:35])=[CH:13][CH:12]=4)=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 115623-BromoanilineHCID 2734318(3-Bromophenyl)boronic acidHCID 114995954-Chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidineHCID 22484500HCID 22484500, compound

Product 1

HCID 18473296HCID 18473296, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Utilizing an analogous procedure as described in Example 26, 4-chloro-(5-phenyl)-7H-pyrrolo[2,3-d] pyrimidine, the intermediate, was made in 74% yield from 7-benzenesulfonyl-4-chloro-5iodo-7H-pyrrolo[2,3-d]pyrimidine and 3-bromo benzene boronic acid: TS-MS: 230 (MH+) This second intermediate was coupled with 3-bromoaniline in methanol in a sealed tube to provide (3-bromo-phenyl)-[5-(4-chloro-phenyl)7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine in 75% yield: TSMS: 365 (MH+). (3-bromo-phenyl)-[5-(4-chloro-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine was brominated with N-bromosuccinimide impregnated onto silica gel. The reaction was complete after stirring at room temperature under nitrogen for 1.5 hours. The reaction was filtered and concentrated in vacuo to provide the title compound as a gray solid in 28% yield (128 mg): MP.: dec 300° C.; TSMS: 445/447 (MH+/MH+2); anal. RP1 8-HPLC RT=7.223 minutes.

Sources & evidence

ORD record
ord-fb4b308f46904362b7541cac19a74eab
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

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