Bicarbonate Ion → 2-cyclopentyl-4-(3-hydroxyprop-1-ynyl)-5-(6-(trifluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamido)phenyl methyl carbonate

HRID 684880Notes

Reaction equation

HRID 684880 reaction equation
[C:1]([O:2][c:3]1[c:4]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:5][c:6]([Br:27])[c:7]([NH:9][C:10](=[O:11])[CH:12]2[CH2:13][NH:14][c:15]3[c:16]([cH:18][cH:19][c:20]([O:22][C:23]([F:24])([F:25])[F:26])[cH:21]3)[O:17]2)[cH:8]1)([O:33][CH3:34])=[O:35].[CH3:36][CH2:37][N:38]([CH2:39][CH3:40])[CH2:41][CH3:42].[Cu:98][I:99].[Na+:51].[O-:47][C:48]([OH:49])=[O:50].[O:52]=[CH:53][N:54]([CH3:55])[CH3:56].[OH:43][CH2:44][C:45]#[CH:46].[Pd:57]([Cl:58])[Cl:59].[c:60]1([P:61]([c:62]2[cH:63][cH:64][cH:65][cH:66][cH:67]2)[c:68]2[cH:69][cH:70][cH:71][cH:72][cH:73]2)[cH:74][cH:75][cH:76][cH:77][cH:78]1.[c:79]1([P:80]([c:81]2[cH:82][cH:83][cH:84][cH:85][cH:86]2)[c:87]2[cH:88][cH:89][cH:90][cH:91][cH:92]2)[cH:93][cH:94][cH:95][cH:96][cH:97]1>>[C:1]([O:2][c:3]1[c:4]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:5][c:6]([C:46]#[C:45][CH2:44][OH:43])[c:7]([NH:9][C:10](=[O:11])[CH:12]2[CH2:13][NH:14][c:15]3[c:16]([cH:18][cH:19][c:20]([O:22][C:23]([F:24])([F:25])[F:26])[cH:21]3)[O:17]2)[cH:8]1)([O:33][CH3:34])=[O:35]

Participants

10

Reactant 9

HCID 769Bicarbonate IonHCID 923Sodium ionHCID 6228DimethylformamideHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 593949824-Bromo-2-cyclopentyl-5-(6-(trifluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamido)phenyl methyl carbonate

Product 1

HCID 593949372-cyclopentyl-4-(3-hydroxyprop-1-ynyl)-5-(6-(trifluoromethoxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxamido)phenyl methyl carbonate

Sources & evidence

ORD record
ord-e42a146c3576475ba968e5877fd7d345
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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