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Dimethylformamide → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851775
Notes
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Reaction equation

HRID 1851775 reaction equation
CO[C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16](C(N)=O)=[N:17][CH:18]=1.[CH3:22][O:23]C1C=CC2N=C(C3C=CC(C(F)(F)F)=CN=3)SC=2C=1.[CH3:43][N:44](C=O)C>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:22][O:23][C:11]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:13]3[CH:14]=[CH:15][C:16]([NH:44][CH3:43])=[N:17][CH:18]=3)=[N:7][C:6]=2[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 3501866-MethoxybenzothiazoleHCID 7351515-Bromopyridine-2-carboxamideHCID 248038916-Methoxy-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazole

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 2734558
Bis(tri-tert-butylphosphine)palladium(0)
Catalyst

Procedure

6-Methoxy-1,3-benzothiazole (0.100 g, 0.61 mmol) and 5-bromopyridine-2-carboxamide (0.146 g, 0.73 mmol) were reacted according to the procedure used for the preparation of 6-methoxy-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazole, with the following exceptions: 10 mol % bis(tri-t-butylphosphine) palladium (0) was used and the amount of DMF was reduced (3 mL). The reaction mixture was concentrated and flash chromatography of the residue gave the title compound (10 mg) as an off-white solid. 1H NMR δ 9.25 (dd, 1 H) 8.56 (dd, 1 H) 8.23 (br s, 1 H) 8.19 (dd, 1 H) 8.04 (d, 1 H) 7.81 (d, 1H) 7.78 (br s, 1 H) 7.20 (dd, 1 H) 3.88 (s, 3 H); MS ink (M+H) 286.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1f368683f64b428a84477d73c592dfd2
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes