Bromide ion → Tert-butyl 6-(1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate

HRID 2135663Notes

Reaction equation

HRID 2135663 reaction equation
[Br-:47].[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[n:7]1.[CH2:41]1[O:42][CH2:43][CH2:44][O:45][CH2:46]1.[CH3:15][N:16]1[CH2:17][CH2:18][NH:19][c:20]2[cH:21][c:22]([B:26]3[O:27][C:28]([CH3:29])([CH3:30])[C:31]([CH3:32])([CH3:33])[O:34]3)[cH:23][cH:24][c:25]21.[CH3:48][CH2:49][CH2:50][CH2:51][N+:52]([CH2:53][CH2:54][CH2:55][CH3:56])([CH2:57][CH2:58][CH2:59][CH3:60])[CH2:61][CH2:62][CH2:63][CH3:64].[K+:35].[K+:36].[O-:37][C:38]([O-:39])=[O:40].[OH2:65].[Pd:66]([Cl:67])[Cl:68].[c:69]1([P:70]([c:71]2[cH:72][cH:73][cH:74][cH:75][cH:76]2)[c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[cH:83][cH:84][cH:85][cH:86][cH:87]1.[c:88]1([P:89]([c:90]2[cH:91][cH:92][cH:93][cH:94][cH:95]2)[c:96]2[cH:97][cH:98][cH:99][cH:100][cH:101]2)[cH:102][cH:103][cH:104][cH:105][cH:106]1>>[c:2]1(-[c:22]2[cH:21][c:20]3[c:25]([cH:24][cH:23]2)[N:16]([CH3:15])[CH2:17][CH2:18][NH:19]3)[cH:3][cH:4][cH:5][c:6]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[n:7]1

Participants

11

Reactant 10

HCID 259Bromide ionHCID 813Potassium Cation2×HCID 962WaterHCID 11776Triphenylphosphine2×HCID 16028TetrabutylammoniumHCID 19660Carbonate IonHCID 24290Palladium ChlorideHCID 312751,4-DioxaneHCID 23432991tert-Butyl 6-bromopicolinateHCID 594187141-Methyl-1,2,3,4-tetrahydroquinoxaline-6-boronic Acid Pinacol Ester

Product 1

HCID 59418755Tert-butyl 6-(1-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)picolinate

Sources & evidence

ORD record
ord-311eb7536a0e4462b1aa17046a32bccd
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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