Hydrochloric Acid → 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

HRID 196458

Reaction equation

HRID 196458 reaction equation
[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]([Br:17])[cH:14][cH:15][c:16]12.[CH2:18]([CH2:19][CH2:20][C:21]#[CH:22])[OH:23].[CH2:26]1[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]1.[ClH:25].[Cu:109][I:110].[OH2:24].[Pd:32].[c:33]1([P:34]([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48][cH:49][cH:50][cH:51]1.[c:52]1([P:53]([c:54]2[cH:55][cH:56][cH:57][cH:58][cH:59]2)[c:60]2[cH:61][cH:62][cH:63][cH:64][cH:65]2)[cH:66][cH:67][cH:68][cH:69][cH:70]1.[c:71]1([P:72]([c:73]2[cH:74][cH:75][cH:76][cH:77][cH:78]2)[c:79]2[cH:80][cH:81][cH:82][cH:83][cH:84]2)[cH:85][cH:86][cH:87][cH:88][cH:89]1.[c:90]1([P:91]([c:92]2[cH:93][cH:94][cH:95][cH:96][cH:97]2)[c:98]2[cH:99][cH:100][cH:101][cH:102][cH:103]2)[cH:104][cH:105][cH:106][cH:107][cH:108]1>>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][c:11]2[cH:12][c:13]([C:22]#[C:21][CH2:20][CH2:19][CH2:18][OH:23])[cH:14][cH:15][c:16]12

Participants

9

Reactant 8

HCID 313Hydrochloric AcidHCID 962WaterHCID 8082PiperidineHCID 11776Triphenylphosphine4×HCID 23938PalladiumHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 793464-Pentyn-1-olHCID 2728482N-Boc-5-bromoindole

Product 1

HCID 695483925-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-b5d167568a424684b7277fd33e14a471
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Linked notes

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