Potassium Carbonate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-indazol-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)ethanol

HRID 510288Notes

Reaction equation

HRID 510288 reaction equation
C(OC[C@H]([C:15]1[C:24](C)=[CH:23][C:18]2[N:19]=[C:20](Br)S[C:17]=2[C:16]=1C1C=CC(Cl)=CC=1)OC(C)(C)C)(=O)C(C)(C)C.Cl[C:34]1C=C(B(O)O)C=C[N:35]=1.C(=O)([O-])[O-].[K+].[K+].C([O:55][CH2:56][C@@H:57]([O:82][C:83]([CH3:86])([CH3:85])[CH3:84])[C:58]1[C:73]([CH3:74])=[CH:72][C:61]2[N:62]=[C:63]([C:65]3[CH:70]=[CH:69][N:68]=[C:67](Cl)[CH:66]=3)[S:64][C:60]=2[C:59]=1[C:75]1[CH:80]=[CH:79][C:78]([Cl:81])=[CH:77][CH:76]=1)(=O)C(C)(C)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:83]([O:82][C@@H:57]([C:58]1[C:73]([CH3:74])=[CH:72][C:61]2[N:62]=[C:63]([C:65]3[CH:70]=[CH:69][N:68]=[C:67]([C:24]4[CH:23]=[C:18]5[C:17]([CH:34]=[N:35][N:19]5[CH3:20])=[CH:16][CH:15]=4)[CH:66]=3)[S:64][C:60]=2[C:59]=1[C:75]1[CH:80]=[CH:79][C:78]([Cl:81])=[CH:77][CH:76]=1)[CH2:56][OH:55])([CH3:85])([CH3:84])[CH3:86]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 86699798(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalateHCID 86699799(S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate2×

Product 1

HCID 86699820(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-indazol-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)ethanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (0.190 g, 0.35 mmol), 2-chloropyridin-4-ylboronic acid (0.66 g, 0.42 mmol), Pd(PPh3)4 (0.020 g, 0.0175, aq. 2M potassium carbonate solution (0.7 mL, 1.4 mmol) in degassed dioxane (2.0 mL) was heated at 90° C. for 3 hr. LC/MS indicated a 1.5:1 ratio of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate to (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate. Reaction mixture was used in next step without further purification.

Workup

  1. customReaction mixture
  2. customwas used in next step without further purification

Sources & evidence

ORD record
ord-e7b798dd8e3a43f59c39e285d0f4a6d2
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

Loading…