5-Chloro-2-methoxyphenylboronic acid → HCID 67243851, compound

HRID 2422880Notes

Reaction equation

HRID 2422880 reaction equation
C(C1C=C(C(N)C)C=CC=1C1C=C(F)C=CC=1OC)C=C.BrC1C=CC(C(N)C)=C(Cl)C=1.ClC1C=CC(OC)=C(B(O)O)C=1.FC1C=C(C2C=C(F)C=CC=2OC)C=CC=1C(NS(C1C(C(F)(F)F)=NN(C)C=1)(=O)=O)C.[Cl:77][C:78]1[CH:79]=[CH:80][C:81]([O:94][CH3:95])=[C:82]([C:84]2[CH:89]=[CH:88][C:87]([CH:90]([NH2:92])[CH3:91])=[C:86]([F:93])[CH:85]=2)[CH:83]=1.[F:96][C:97]1[CH:98]=[C:99]([S:104](Cl)(=[O:106])=[O:105])[CH:100]=[CH:101][C:102]=1[F:103]>>[Cl:77][C:78]1[CH:79]=[CH:80][C:81]([O:94][CH3:95])=[C:82]([C:84]2[CH:89]=[CH:88][C:87]([CH:90]([NH2:92])[CH3:91])=[C:86]([F:93])[CH:85]=2)[CH:83]=1.[Cl:77][C:78]1[CH:79]=[CH:80][C:81]([O:94][CH3:95])=[C:82]([C:84]2[CH:89]=[CH:88][C:87]([CH:90]([NH:92][S:104]([C:99]3[CH:100]=[CH:101][C:102]([F:103])=[C:97]([F:96])[CH:98]=3)(=[O:106])=[O:105])[CH3:91])=[C:86]([F:93])[CH:85]=2)[CH:83]=1

Participants

8

Reactant 6

HCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 598430341-(4-Bromo-2-chlorophenyl)ethanamineHCID 67243851HCID 67243851, compoundHCID 67244664HCID 67244664, compoundHCID 672454371-Methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonic acid [1-(3,5'-difluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-amide

Product 2

HCID 67243851HCID 67243851, compoundHCID 67244524HCID 67244524, compound

Procedure

1-(5′-Chloro-3-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine was prepared in a similar manner to 1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (Example 34) using 1-(4-bromo-2-chloro-phenyl)-ethylamine instead of 1-(4-bromo-2-fluoro-phenyl)-ethylamine and 5-chloro-2-methoxyphenyl boronic acid instead of 5-fluoro-2-methoxyphenyl boronic acid. The title compound was prepared in a similar manner to 1-methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonic acid [1-(3,5′-difluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-amide (Example 30) using 1-(5′-chloro-3-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine and 3,4-di-fluorophenyl sulfonyl chloride instead of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-sulfonyl chloride. 1H NMR (400 MHz, CDCl3): δ 7.55-7.41 (m, 2H), 7.28 (q, 1H), 7.17 (d, 1H), 7.12-6.99 (m, 4H), 6.89 (d, 1H), 5.16 (d, 1H), 4.73 (dq, 1H), 3.80 (s, 3H), 1.55 (d, 3H) ppm; MS (ESI) m/z: 478.0 [M+Na]+.

Sources & evidence

ORD record
ord-27b9baef2e7341d899f5cdff9aece8a1
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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