5-Methylindoline → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-methylindolin-1-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879466

Reaction equation

HRID 879466 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15](C3C=CN=C(N4CC5C=CN=CC=5C4=O)C=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].BrC1SC2C(C3C=CC(Cl)=CC=3)=C([C@H](OC(C)(C)C)C(OCC)=O)C(C)=CC=2N=1.[CH3:72][C:73]1[CH:74]=[C:75]2[C:79](=[CH:80][CH:81]=1)[NH:78][CH2:77][CH2:76]2.C1C2C=CN=CC=2C(=O)N1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([N:78]3[C:79]4[C:75](=[CH:74][C:73]([CH3:72])=[CH:81][CH:80]=4)[CH2:76][CH2:77]3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 140236795-MethylindolineHCID 205051661,2-Dihydro-3H-pyrrolo(3,4-c)pyridin-3-oneHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700276(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

Product 1

HCID 86700277(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-methylindolin-1-yl)benzo[d]thiazol-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-methylindolin-1-yl)benzo[d]thiazol-6-yl)acetic acid was prepared in similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-oxo-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid except (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate was used instead of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate, 5-Methylindoline was used instead 1H-pyrrolo[3,4-c]pyridin-3(2H)-one and Pd(P-tBu3)2 was used instead of Pd2(dba)3. LCMS-ESI+: C29H30ClN2O3S: 521.2 (M+H+); Found: 521.2 (M+H+); 1H NMR (400 MHz, CD3OD) δ: 7.75 (s, 1H), 7.67-7.64 (m, 1H), 7.57-7.50 (m, 3H), 7.44 (s, 1H), 7.12 (d, 1H), 6.84 (d, 1H), 5.17 (s, 1H), 4.07 (dd, 2H), 3.19 (dd, 2H), 2.53 (s, 3H), 2.35 (s, 3H), 0.95 (s, 9H).

Sources & evidence

ORD record
ord-00be1056b0d14a0cb68a27ec482d8569
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Linked notes

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