2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridine → (1SR,3RS)-3-[3-(2-Chloro-6-fluoro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

HRID 383318Notes

Reaction equation

HRID 383318 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([F:17])[N:3]=1.ClC1C=C([C:25]2[N:29]3[CH:30]=[C:31]([NH:34][CH:35]4[CH2:40][CH2:39][CH2:38][CH:37]([OH:41])[CH2:36]4)[CH:32]=[CH:33][C:28]3=[N:27][CH:26]=2)C=CN=1.BrC1N2C=C(NC3CCCC(O)C3)C=CC2=NC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:25]2[N:29]3[CH:30]=[C:31]([NH:34][CH:35]4[CH2:40][CH2:39][CH2:38][CH:37]([OH:41])[CH2:36]4)[CH:32]=[CH:33][C:28]3=[N:27][CH:26]=2)[CH:5]=[C:4]([F:17])[N:3]=1

Participants

4

Reactant 3

HCID 467392412-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridineHCID 68483082(1RS,3RS)-3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanolHCID 86644340(1SR,3RS)-3-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol2×

Product 1

HCID 86644342(1SR,3RS)-3-[3-(2-Chloro-6-fluoro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

Procedure

The title compound is prepared from 2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine and (1SR,3RS)-3-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol [Intermediate R (step 1)] by a procedure analogous to [Intermediate J (step 2)]

Sources & evidence

ORD record
ord-ee9a8f5776c04425a4648c563be0f223
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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