Dimethylformamide → [4-(3-cyclopropylethynyl-1-cyclopropylmethyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester

HRID 2334131Notes

Reaction equation

HRID 2334131 reaction equation
[CH3:36][CH2:37][N:38]([CH2:39][CH3:40])[CH2:41][CH3:42].[CH3:48][CH2:49][O:50][C:51]([CH3:52])=[O:53].[CH:1]([CH3:2])([CH3:3])[O:4][C:5]([NH:6][c:7]1[cH:8][cH:9][c:10](-[c:13]2[n:14]([CH2:26][CH:27]3[CH2:28][CH2:29]3)[c:15]3[cH:16][c:17]([O:23][CH2:24][CH3:25])[cH:18][cH:19][c:20]3[c:21]2[I:22])[cH:11][cH:12]1)=[O:30].[CH:31]1([C:34]#[CH:35])[CH2:32][CH2:33]1.[Cu:95][I:96].[O:43]=[CH:44][N:45]([CH3:46])[CH3:47].[Pd:54]([Cl:55])[Cl:56].[c:57]1([P:58]([c:59]2[cH:60][cH:61][cH:62][cH:63][cH:64]2)[c:65]2[cH:66][cH:67][cH:68][cH:69][cH:70]2)[cH:71][cH:72][cH:73][cH:74][cH:75]1.[c:76]1([P:77]([c:78]2[cH:79][cH:80][cH:81][cH:82][cH:83]2)[c:84]2[cH:85][cH:86][cH:87][cH:88][cH:89]2)[cH:90][cH:91][cH:92][cH:93][cH:94]1>>[CH:1]([CH3:2])([CH3:3])[O:4][C:5]([NH:6][c:7]1[cH:8][cH:9][c:10](-[c:13]2[n:14]([CH2:26][CH:27]3[CH2:28][CH2:29]3)[c:15]3[cH:16][c:17]([O:23][CH2:24][CH3:25])[cH:18][cH:19][c:20]3[c:21]2[C:35]#[C:34][CH:31]2[CH2:32][CH2:33]2)[cH:11][cH:12]1)=[O:30]

Participants

9

Reactant 8

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 138823CyclopropylacetyleneHCID 59425548[4-(1-cyclopropylmethyl-6-ethoxy-3-iodo-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester

Product 1

HCID 59425623[4-(3-cyclopropylethynyl-1-cyclopropylmethyl-6-ethoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester

Sources & evidence

ORD record
ord-2fa7aa5a6129417ab06648cb9ef884eb
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (10/10)

Reaction notes

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