Potassium Fluoride → Ethyl 4-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetate

HRID 1926374Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14](Br)[CH:15]=1.[CH2:18]([O:20][C:21](=[O:33])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[CH3:19].[F-].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:17][C:11]1[N:12]=[CH:13][C:14]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:33])=[CH:25][CH:26]=2)=[CH:15][C:10]=1[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (100 mg, 0.330 mmol), 4-(2-ethoxy-2-oxoethoxy)benzeneboronic acid (100 mg, 0.600 mmol) and potassium fluoride (57 mg, 0.98 mmol) in 1,4-dioxane (9.0 mL) and H2O (3.0 mL) was degassed and refilled with argon (3×) prior to the addition of Pd(dppf)Cl2 (10 mg, 0.020 mmol). The reaction mixture was degassed and refilled with argon (2×) and left to stir at 100° C. for 2 h. The mixture was quickly passed through a silica gel pad (5% MeOH in DCM), which afforded the title compound as a yellow solid. MS (ES+): m/z=406.10 (100) [MH+]. HPLC: tR=3.90 min (ZQ3, polar—5 min).

Workup

customwas degassed
additionrefilled with argon (3×)
customThe reaction mixture was degassed
additionrefilled with argon (2×)
waitleft

Sources & evidence

ORD record: ord-68d7079f2c764972a885c9491515b490
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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