{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}boronic acid → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzo[d]thiazol-6-yl)acetate

HRID 879571Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([C:19]3[CH:27]=[C:26]4C([C:23]([CH3:29])=[N:24][N:25]4C)=[CH:21][CH:20]=3)[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].CC1N2C=CC(B(O)O)=CC2=N[N:42]=1>>[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[CH:21][N:42]4[C:23]([CH3:29])=[N:24][N:25]=[C:26]4[CH:27]=3)[S:18][C:14]=2[C:13]=1[C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 75485741{3-Methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl}boronic acid

HCID 86700213(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700392(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzo[d]thiazol-6-yl)acetate

Procedure

Prepared in a manner similar to (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-indazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate, but using 3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-ylboronic acid instead of 1,3-dimethyl-1H-indazol-6-ylboronic acid. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.94 (d, J=6.0 Hz, 1H), 7.91 (s, 1H), 7.75 (s, 1H), 7.58-7.49 (m, 3H), 7.49-7.44 (m, 1H), 5.17 (s, 1H), 4.26-4.16 (m, 2H), 2.81 (s, 3H), 2.61 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 0.98 (s, 9H).

Sources & evidence

ORD record: ord-fed78cd6b3454ce98a300e81d2a34bca
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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