5-Chloro-2-methoxyphenylboronic acid → (r)-3,4-Difluorobenzenesulfonic acid [1-(5'-chloro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

HRID 2422866Notes

Reaction equation

HRID 2422866 reaction equation
ClC1C=C(C2C=CC([C@H](N)C)=CC=2)C(OC)=NC=1.BrC1C=CC([C@H](NC(=O)O)C)=CC=1.ClC1C=CC(OC)=C(B(O)O)C=1.[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([O:60][CH3:61])=[C:49]([C:51]2[CH:56]=[CH:55][C:54]([C@H:57]([NH2:59])[CH3:58])=[CH:53][CH:52]=2)[CH:50]=1.[F:62][C:63]1[CH:64]=[C:65]([S:70](Cl)(=[O:72])=[O:71])[CH:66]=[CH:67][C:68]=1[F:69]>>[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([O:60][CH3:61])=[C:49]([C:51]2[CH:56]=[CH:55][C:54]([C@H:57]([NH2:59])[CH3:58])=[CH:53][CH:52]=2)[CH:50]=1.[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([O:60][CH3:61])=[C:49]([C:51]2[CH:56]=[CH:55][C:54]([C@H:57]([NH:59][S:70]([C:65]3[CH:66]=[CH:67][C:68]([F:69])=[C:63]([F:62])[CH:64]=3)(=[O:72])=[O:71])[CH3:58])=[CH:53][CH:52]=2)[CH:50]=1

Participants

7

Reactant 5

HCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 58923092(r)-[1-(4-Bromophenyl)-ethyl]-carbamic acidHCID 67244310HCID 67244310, compoundHCID 67245059(r)-1-(5'-Chloro-2'-methoxy-biphenyl-4-yl)-ethylamine

Product 2

HCID 67244367(r)-3,4-Difluorobenzenesulfonic acid [1-(5'-chloro-2'-methoxy-biphenyl-4-yl)-ethyl]-amideHCID 67245059(r)-1-(5'-Chloro-2'-methoxy-biphenyl-4-yl)-ethylamine

Procedure

(R)-1-(5′-Chloro-2′-methoxy-biphenyl-4-yl)-ethylamine was prepared in a similar manner to (R)-1-[4-(5-chloro-2-methoxypyridin-3-yl)-phenyl]ethylamine (Example 39) starting from (R)-[1-(4-bromophenyl)-ethyl]-carbamic acid and 5-chloro-2-methoxyphenylboronic acid. The title compound was prepared in a similar manner to (R)-1-Methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonic acid 1-{[4-(5-chloro-2-methoxypyridin-3-yl)-phenyl]-ethyl}-amide (Example 39) using (R)-1-(5′-chloro-2′-methoxy-biphenyl-4-yl)-ethylamine and 3,4-difluorobenzenesulfonyl chloride. 1H NMR (400 MHz, CDCl3): 7.52-7.42 (m, 2H), 7.35-7.08 (m, 7H), 6.90 (m, 1H), 4.80 (d, 1H), 4.60 (q, 1H), 3.79 (s, 3H), 1.51 (d, 3H) ppm.

Sources & evidence

ORD record
ord-e0b8577bb053485a967c4ae70b523624
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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