4-Chlorophenylboronic acid → HCID 18473286, compound

HRID 2227257Notes

Reaction equation

HRID 2227257 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14](OC)=[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:37])C=3C(I)=C2)(=O)=O)C=CC=CC=1.ClC1C=CC(B(O)O)=CC=1.[NH2:49][C:50]1[CH:51]=[C:52]([C:56]#[CH:57])[CH:53]=[CH:54][CH:55]=1>>[Cl:37][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:49][C:50]4[CH:55]=[CH:54][CH:53]=[C:52]([C:56]#[CH:57])[CH:51]=4)=[N:7][CH:6]=[N:5][C:4]=3[NH:8][CH:9]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 104682Benzenamine, 3-ethynyl-HCID 18473263HCID 18473263, compoundHCID 22484500HCID 22484500, compound

Product 1

HCID 18473286HCID 18473286, compoundYield 33%

Procedure

Following the procedure described in Example 26, 4-chloro-[5-(4-methoxy-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 4-chloro benzene boronic acid: TS-MS: 260 (MH+). The title compound was synthesized by coupling the intermediate with m-aminophenyl acetylene in 33% yield: MP: 225-227° C.; TSMS: 398 (MH+); anal. RP18-HPLC RT=6.45 minutes.

Sources & evidence

ORD record
ord-c5e1e91504b747e29740efe83d9990ab
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

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