Benzoic Acid → HCID 67521429, compound

HRID 1926367Notes

Reaction equation

HRID 1926367 reaction equation
COC(=O)C1C=C[CH:7]=[C:6]([C:10]2[CH:11]=[N:12][C:13]([NH2:25])=[C:14]([C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH:15]=2)[CH:5]=1.C(O)(=O)C1C=CC=CC=1.S1C2C=CC=CC=2N=C1C1C(N)=NC=C(Br)C=1.C[O:54][C:55]([C:57]1[CH:62]=CC(B2OC(C)(C)C(C)(C)O2)=C[N:58]=1)=[O:56].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.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>[NH2:25][C:13]1[N:12]=[CH:11][C:10]([C:6]2[CH:5]=[N:58][C:57]([C:55]([OH:56])=[O:54])=[CH:62][CH:7]=2)=[CH:15][C:14]=1[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

8

Reactant 5

HCID 243Benzoic AcidHCID 10796Cesium carbonateHCID 467386632-Methoxycarbonyl-5-pyridineboronic acid, pinacol esterHCID 67389127HCID 67389127, compoundHCID 67520373HCID 67520373, compound

Product 1

HCID 67521429HCID 67521429, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

Following the procedures for 3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester and the benzoic acid, the title compound was prepared from 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (1.1 g, 3.6 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid methyl ester (1.0 g, 3.8 mmol), Pd(PPh3)4 (2 mol %), and Cs2CO3 (2.83 g, 8.7 mmol) in DMF/H2O (24 mL, 5:1). 1H NMR (400 MHz, DMSO-d6): δ=8.90 (s, 1H), 8.61 (d, J=2.0 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.20-8.07 (m, 5H), 7.96 (brd, J=8.4 Hz, 1H), 7.57 (dt, J=1.0, 8.0 Hz, 1H), 7.49 (dt, J=1.0, 8.0 Hz, 1H); COOH proton not visible. MS(ES+): m/z=349.08 (100) [MH+], 305.09 (8) [MH+—CO2]. HPLC: tR=2.89 min (polar—5 min, ZQ3).

Workup

  1. customHPLC: tR=2.89 min (polar—5 min, ZQ3)

Sources & evidence

ORD record
ord-b757b3f00f24413883242e59ee7b5dff
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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