Acetate → tert-Butyl 5-cyclopropylpicolinate

HRID 308320Notes

Reaction equation

[Br:34][c:35]1[cH:36][cH:37][c:38]([C:41](=[O:42])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[n:39][cH:40]1.[C:56]([O-:57])(=[O:58])[CH3:59].[C:61]([O-:62])(=[O:63])[CH3:64].[CH3:48][c:49]1[cH:50][cH:51][cH:52][cH:53][cH:54]1.[CH:1]1([B:4]([OH:5])[OH:6])[CH2:2][CH2:3]1.[CH:7]1([P:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.[K+:31].[K+:32].[K+:33].[OH2:55].[P:26]([O-:27])([O-:28])([O-:29])=[O:30].[Pd+2:60]>>[CH:1]1([c:35]2[cH:36][cH:37][c:38]([C:41](=[O:42])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[n:39][cH:40]2)[CH2:2][CH2:3]1

Participants

Reactant 9

HCID 175Acetate2×

HCID 813Potassium Cation3×

HCID 962Water

HCID 1061Phosphate

HCID 1140Toluene

HCID 75806Tricyclohexylphosphine

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)

HCID 2760897Cyclopropylboronic acid

HCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

Product 1

HCID 57827284tert-Butyl 5-cyclopropylpicolinate

Sources & evidence

ORD record: ord-4ebad60717484c85a9bf4ceef4cee211
Source dataset: Training data from https://doi.org/10.1039/C8SC04228D (8/10)
DOI: 10.1039/C8SC04228D

Reaction notes

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