3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → HCID 86717269, compound

HRID 588569Notes

Reaction equation

HRID 588569 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH2:3][CH2:2]1.[Cl:16][C:17]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:21][N:20]=[C:19]2[N:29]([CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][C@@H:37]([F:40])[CH2:36]3)[N:30]=[C:31](I)[C:18]=12>>[Cl:16][C:17]1[C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:21][N:20]=[C:19]2[N:29]([CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][C@@H:37]([F:40])[CH2:36]3)[N:30]=[C:31]([C:4]3[CH2:3][CH2:2][O:1][CH2:6][CH:5]=3)[C:18]=12

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86717270HCID 86717270, compound

Product 1

HCID 86717269HCID 86717269, compound

Procedure

Compound Iq was synthesized according to Example 1, but using 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-chloro-1-[2-[(3R)-3-fluoropyrrolidin-1-yl]ethyl]-3-iodo-5-phenyl-pyrazolo[3,4-c]pyridazine instead of 4-chloro-3-iodo-1-(2-(4-methylpiperazin-1-yl)ethyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazine in Step 8.

Workup

  1. customCompound Iq was synthesized

Sources & evidence

ORD record
ord-69cdaf100a5a45f4a0974eda280486e1
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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